Confession: The Miles I Missed and Mistakes I’ve Made

I think it’s useful to share my mistakes as well as my successes. One thing I’ve learned is that for people to take advantage of the offers right in front of them it needs to seem achievable. Even when I’ve been willing to walk work colleagues through everything start to finish I’ve heard people talk about travel all over the world in premium cabins as “a Gary thing” as though there’s some magic difference between us.

I’m far from perfect and exposing that may also help show that it’s all a learning process, trial and error, and that it doesn’t take anything other than being human and paying attention to improve your travel skills and jump on deals that come along.

I failed to earn miles when I was younger, even failed to have an account when I first flew enough to earn elite status. I’ve let miles expire. And I broke some program rules two decades ago without even realizing it was a big deal. These are stories I’ve shared before but not in any kind of systematic way in a couple of years.

My High School and College Miles

I debated in high school and at the start (and then the very end) of college, and saw some success at the national level. I should have been earning points. I wasn’t.

As a high school debater travel was mostly driving in-state — though I did fly to North Dakota for Nationals. We waited too long to book our tickets and couldn’t get flights into Fargo, so we wound up flying Northwest via Minneapolis to Grand Forks, North Dakota and driving. I just remember feeling like we were at ground zero in the event of a Soviet pre-emptive nuclear strike, because of the likelihood of nearby missile silos. It’s strange the things you thought of back then. Boris Yeltsin had stood atop a tank months earlier but I don’t think that had yet changed everything I had heard growing up as a kid.

We stayed at the Madison hotel in Moorhead, Minnesota just outside of Fargo. J.J. Walker was performing in the lounge. But I wasn’t aware of any points opportunities. Many of the hotels we stayed in didn’t have loyalty programs then and I certainly wasn’t aware of them.

I signed up for my first frequent flyer program as a teenager before a trip to Australia. I flew American Airlines to Sydney via Honolulu and earned almost enough miles for a free domestic roundtrip award. Those miles ultimately expired, unused.

My freshman year of college I debated for UCLA, and that started out as a phenomenal experience. The team had won CEDA nationals the previous year. They were ultra-competitive, and the work ethic was intense. I soaked in tremendous learning.

Driving back from the UNLV tournament during the winter quarter several of my teammates were involved in a van crash. (I was driving my own car just a little behind that van.)

My partner through much of the season was killed. That cut short most of my own debating, but I did continue to travel a little bit for competition and I traveled as a coach.

I went to CEDA nationals at Towson State University in Maryland my freshman year anyway and did well (without much in the way of materials, our boxes were destroyed in the crash) that was for the most part the end of my debate career. I did compete successfully in parliamentary debate in a national tournament at the end of my senior year at the University of Alabama, Tuscaloosa (I lost the final round), the only time I competed in that event. But I only flew to two tournaments as a college debater after the crash.

My last three years of college, though, I coached high school debate. I had been a member of a reigning national championship policy debate team, and though our season was cut short I did manage to learn some things along the way that let me offer some skills and strategies to students. My senior year of college the team won the California state championship.

I took my high school teams to tournaments out of state. I mostly remember driving 15 passenger vans rented from Enterprise, and staying at hotels that didn’t award points. And didn’t have interior corridors. There weren’t that many points to be earned, but surely I’d have benefited from crediting flights to a frequent flyer program.

Debate today is far more electronic than it was then. I recall carrying a Mac onboard flights in 1992 and 1993. And I couldn’t imagine paying checked bag fees for all of the tubs of ‘evidence’ we used to carry around on carts. It’s a good thing airlines didn’t charge for checked bags in those days.


Image: New York Times

My senior year of college I easily flew enough to earn elite status. There were at least 4 California – DC roundtrips, California – Florida, California – Alabama, and more. Yet it never occurred to me to sign up for programs or credit miles to an account. My American miles had already expired — I hadn’t played around with miles and points for five years and didn’t again I started working. (Flying back from Alabama to California in 1996 I remember one person on the team signing up at the airport for AAdvantage but I didn’t stop to think much more about it.)

I Started Paying Attention Once I Graduated College

I’m not sure what prompted me to join a frequent flyer program back in 1996. I think that’s when I joined the United and US Airways program. I was certainly flying for work, and suddenly I was aware of the program marketing. I used some of my family’s British Airways miles to fly home to California for Thanksgiving on American, and that certainly underscored the value of miles and points for me.

I remember calling up United on the phone after each trip to hear my mileage balance, and see if flights had posted yet. I loved to hear that number grow from the automated Mileage Plus system. Back when I had 60,000 and then 90,000 miles in the account that seemed like a lot (of course 90,000 was enough for a business class roundtrip to Australia back then, with much better availability than we see today).

At the time I also stumbled onto a book one day browsing the shelves in a Barnes & Noble that set me off on a passionate journey with the airlines: Thomas Petzinger’s Hard Landing: The Epic Contest For Power And Profits That Plunged The Airlines Into Chaos, a great book on the business history of the US airline industry from inception through the mid-1990s (still probably the best book on the industry I’ve ever read).

My first full year out of school was 1997 and I earned elite status on United. I quickly figured out that even as a first-tier Premier member I could reliably upgrade if I avoided first flight Monday morning and Thursday and Friday evenings. I went for the big planes flying domestically — 747s and 777s back then! — and would almost always clear. I cared enough about the upgrade that I’d even try to stick myself on San Francisco trips flying 777s through Denver at noon on a Wednesday.

Back then I loved the United Connection disk-based reservations software. I still think that was a more powerful tool than what the bulk of booking websites offer today.

Hitting Premier status made me eligible to participate in United’s iDine program (that required elite status back then!). I remember getting my first bonus offer, miles for eating at four participating restaurants in a limited timeframe. I remember realizing that there was no minimum spend requirement listed at those restaurants, so I could go in and just buy a soda. That’s when I learned the value of reading through fine print.

United didn’t offer unlimited complimentary upgrades then. Upgrade certificates were paper, and checking in at United Express stations those paper upgrade certificates were rarely collected, so they stretched pretty far. You could buy more at a discount on eBay.


Westair United Express Embraer EMB-120

Confirmed domestic upgrades were 10,000 miles with no cash co-pay. United used to inadvertently post class of service mileage bonuses on those. So you’d be earning back most of the miles you spent on a cross country trip. You could also buy confirmed upgrade certificates on eBay which amounted to buying back miles somewhere between one and two cents apiece (although if you used the certificates checking in at a United Express station…).

I wouldn’t buy or sell upgrade certificates now. Back then I just didn’t know any better. Hopefully having purchased upgrade certificates on eBay 21 years ago doesn’t come back to haunt me. The MileagePlus (then ‘Mileage Plus’) terms and conditions don’t include a statute of limitations.

I get asked all the time now, as a result of my award booking service, whether I can help someone buy the miles they need for a trip or if I’d recommend a broker. I won’t get involved in those discussions at all. I just don’t think it’s worth the risk though I’m torn on the appropriateness of the restrictions themselves (value propositions are predicated on a certain amount of breakage which miles sales reduce, but I also do think consumers have a greater moral claim to ownership of their miles than programs generally allow).

I Made Plenty of Mistakes Along the Way

I started getting excited about credit card signup bonuses back in 1997. I remember when a new bonus came out for a Lufthansa card around 2001 and I signed up, not even paying attention to Miles & More’s expiration rules. I earned the bonus, but let those points expire too. So my 1991-earned American AAdvantage miles weren’t the only ones to expire.

Flying on a business class award to Australia in 2000 I visited a club lounge for the first time. I didn’t even realize I had access until I was directed to the United Red Carpet Club in Sydney on the way back. Then I snuck into the Red Carpet Club in Los Angeles before my connecting flight home, not realizing that my arriving boarding pass would have granted me access.

Incidentally it never even occurred to me to redeem miles for first class on that trip, even though I had the points and the increment wasn’t especially great (United charged 90,000 roundtrip for business, 120,000 for first). I never flew international first class until 2005 — 145,000 American AAdvantage miles apiece for Los Angeles – Tahiti (Air Tahiti Nui) // Tahiti – Auckland (Air Tahiti Nui) – Sydney (Qantas) // Melbourne – Los Angeles (Qantas).


Air Tahiti Nui 2-2-2 First Class Seating

And I almost screwed up that booking — I originally had Sydney – Los Angeles on hold, but American called me back to flag that I had held first class award space on an embargoed flight (not all Qantas flights were eligible for AAdvantage redemption then). Fortunately, booking 9 months out, there was Melbourne space home to the States a day later.

It wasn’t until 2002 that I first secured lounge access for real — by status matching to Mexicana Frecuenta Gold, back when the now-defunct airline was a Star Alliance member (they later left for oneworld). My Mexicana card got me into United clubs and I thought that was pretty cool. I took steps to make sure I always had access to lounges after that.

While I like to think I travel pretty well — gliding through the airport effortlessly, handling irregular operations with aplomb — my leisure travel is changing markedly now that I’m a dad. It takes longer to get out of the house (no more 75 minutes front door-to-gate), I wind up checking a bag, and need to be prepared for a bottle and diaper change prior to boarding. That makes me both appreciate my business travel more (traveling like I’m used to) and spending more time at home.

However I’ve made my share of mistakes, by far the biggest was when I showed up at the Sydney airport in the afternoon for a morning flight on Virgin Australia. I showed for the flight time when I originally booked the ticket, not for when it was rescheduled to, even though I had booked a hundred redemptions for people on Virgin Australia’s flight 1 to Los Angeles and knew what time it departed.

I’ve also showed up at the wrong hotel and also made a booking in Bangkok for the wrong month.

I’m Still Far From Perfect

I”m not a maximizing machine. Sometimes I will trade value for comfort and convenience, or give up miles for time saving. I probably place too much value on my time and effort.

But goodness knows I’m having fun!

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. I enjoyed your stories, Gary. My initial involvement in miles-and-points came as a result of signing up, as an afterthought, to PanAm’s FF program — basically figuring it might never produce anything worthwhile but wouldn’t hurt. One business trip to Europe earned me enough miles that, augmented by miles from a First USA Bank “World Card” Master Card, I was able to take a free trip on PanAm to Germany (economy). Soon thereafter, a TWA trip to Israel earned me enough TWA miles for a free domestic economy ticket. I’ve been “playing the game” every since. Your on-line tutoring significantly raised the level of my involvement; my wife and I over the past decade have taken more than a dozen F and C class trips to Europe and Asia.
    Unfortunately, the “golden age” of elite qualification and benefits has passed, but fortunately I was a participant during that age. I had United Premier Gold and Delta Silver Medallion status simultaneously, which resulted in countless upgrades to F on both airlines, both domestically and internationally.
    So far, knock on wood, the worst travel mistake I’ve made is getting the date of arrival in the U.S. after crossing the date line wrong by one day. Fortunately my mistake was to think we would arrive a day later than we did rather than a day earlier. With a nonrefundable ticket booked from LAX to home, we had to spend an unnecessary day and night in LA (but I used a credit card-provided free hotel night, so the cost in $ was minimal). At least a couple of times, your advice to “garden” my reservations has prevented some very unpleasant problems.

  2. So one thing I want to get an idea of is…today, or over the last couple years, how many miles are you earning in a year? I read all these travel blogs with people taking multiple trips in first class for 2 people every year…this is like 750,000+ miles redeeemd every year. Maybe I’m just reading too many blogs and thinking people are traveling more than they are, or these miles are saved up for years then redeemed at once. Or are people really earning 500K+ miles year after year after year?

  3. @Gary love this! I got my first AMEX (corporate card) and Diner’s Club in 1993 (all of my AMEXes say “member since 1993”). I distinctly remember a flyer they passed out – something like “$99 one time fee to join Membership Rewards points.”

    I criss-crossed the country for a few years and never joined MR. The missed points!!

    I then took a job in the early 2000s where I traveled for about 6 years – again on a new company’s AMEX Corporate card. Still no MRs! I came to my senses around 2008 when I bought my first Northwest Airlines WorldPerks card and started down the road of paying attention to points. I’ve taken my wife and five kids on trips many times on miles and points and still get substantial value at the right time.

    One cannot cry over spilled points. But sometimes I do !

  4. Whoa Gary, I had no idea you were on the UCLA team that was in the UNLV crash. That was still talked about all the time when I was debating at USC.

    I also foolishly neglected to earn miles flying to tournaments in high school and college, as well as when I was coaching at a high school in Silicon Valley while I was in grad school. Oh well… I had to go on quite a journey in life before I was on solid enough ground to consider traveling for fun, and I’m sure all my miles would’ve expired by then.

    But it could be worse… my older brother told me about cashing out AAdvantage miles for Target gift cards like it was some kind of travel hack. And he won both the Tournament of Champions and the NFL National tournament in high school.

  5. A great post, Gary! We all learn from our mistakes. My greatest regret was getting a Chase Sapphire card and then not paying attention to the minimum spend deadline, and missing out on the 40K Ultimate Rewards points.

  6. Thanks for the post Gary!

    Many years ago your post on a mistake fare SFO to AKL via SYD in J on UA got me into this game (including buying an upgrade to F on eBay).

    This was after years of collecting and not using Aeroplan miles collected on Youth Standby fares (!). We all had to learn somehow!

  7. @Gary: “It’s a good thing airlines didn’t charge for checked bags in those days.”

    Did the baggage fairy pay for them?

    More likely other passengers paid for yours.

  8. Gary, great stories.
    My first overseas trip was to Europe in June 1970 on one of the then new 747’s – talk about being an excited 20 year old! But I didn’t travel by air after that. I started collecting miles when my husband and I took our first trip by air in 1988 – to Germany 3 years after we got married . I’ll never forget the crazy United promotion – it was called the Half-Fare No-Fare Fare Sale – book a pair tickets where the 2nd was half off (our tickets to Germany) and then book another where the 2nd ticket was free (went to Hawaii).

    At the time of our Hawaii trip, there was another promo offering triple miles for flying 3 segments. Well, we had to deplane for 2 hours in LAX as a connection. United denied the triple miles on the one paid ticket, claiming the 2 legs were the same flight number. I wrote a letter stating that nowhere in the fine print did it state that the segments needed to have different flight numbers and we were off the plane in the middle of the night. Miles awarded!! We used them to fly to Paris in first class the next year! Of course, that’s like domestic 1st these days, but we were in awe, esp. after finding out those tickets were around $14K. Flew home in the nose of a 747 – sweet!

    I didn’t have the kind of job where I traveled for work, only attending an out-of-state conference every few years. But I always tried to collect miles and we used them for coach flights to Europe many times – because I never grasped the concept of using them for upgrades back then. And I remember when the awards came with hotel and rental car certificates – those all went to waste, because my corporate rental car rate was far better, and we always stayed in modest local European hotels. The chain hotels were probably in the same price range back then, but who knew.

    Thanks for bringing back some memories. Yeah, it’s been fun!

  9. I threw away a United Connection CD-ROM before launching as a digital nomad. But I put the software on my google drive before tossing it. Sigh.

  10. A great post, Gary. The reader comments are, by and large, informative and helpful as well.

    My biggest regret was leaving about 27K in USAir miles to expire as the merger with AA was happening. I wonder if there is any way to get them back.

  11. I’m happy that I haven’t made too many mistakes. I flew only one flight without getting miles before signing up on United. I did lose a few car rental opportunities by not signing up for Hertz but choosing airline miles instead. I’ve never had miles expire except a few orphan miles that wasn’t worth saving.

    However, the bottom line is to look forward not backwards.

    Funny, when I first signed up, I thought that I’d never earn enough miles for an award but now have redeemed probably 50 times.

  12. Great recollection Gary .. you’re so open it made me smile. Do you remember the days when if you happened to have a pad of upgrade stickers you could upgrade yourself from Y to F and maybe they’d not catch it; especially if you were underage at the time?

    With so many lamenting the ‘end of an era’; I’m not so sure. Perhaps there will be a rush (more so for personal; but even business to restore and refreshen personal relationships) to travel. I’m counting on the arrival of ‘nose drops’ and single shot ‘antibody therapeutics like Sorrento Therapeutics has in testing right now in Philadelphia, San Diego and Brazil. That way you can get a scrip and any positive test; treat it immediately. NO IV infusion or complexity. Also Sorrento (in particular) has a 2 minute rapid test they filed an EUA for 2 weeks ago and may be approved any day. It’s at home or office so perfect for airlines to use on-the-spot; no special machine and no big time delay. If approved they’ll not be able to keep up with demand; as this is an American inexpensive test; not others. Later you’ll have the Inovia (Defense Dept. backed) vaccine which is DNA and doesn’t require cold temperatures to ship or store; which is a very big deal globally. So yes it’s a drag but we’ll get out of it. By the way in school my Debate topic was ‘should Communist China be allowed to stay in the United Nations’. I guess that’s actually more controversial today 🙂 Happy new year!

  13. Gary, please refresh my memory – before the current “blogs” were introduced, didn’t we wait for the annual, or so, paperback mileage hobby bible that may have produced by Randy? I may be conflating things here.

  14. Great story ..I remember flying like 6 times in one week between LAX and San Diego, in the days of payphones, and I, like you, checked the flights posting upon arrival at each airport on my way to United Gold. That was a lot of fun, and I’ve never looked back.

  15. Thanks Gary…..started flying Western Airlines pre merger; stayed with Delta for untold years and flew LAX/JFK/CDG using the AF Concorde trans Atlantic RT for 160,000 miles all in with domestic FC. Glory day of flying; now retired and still burning thru DL, AS, and AA miles. Thanks again for a great post!

  16. In the early years we are focused on acquiring knowledge. As we make mistakes we gain wisdom . . . at least some do. As an OSU Professor relayed to me, “never ever confuse knowledge with wisdom.”

  17. I guess that I should be proud to say that by the time I finished grad school at UCLA I had – through careful planning – enough CO miles to fly to Europe and back (which was fine as I had not yet experienced C/F).

    My biggest mistakes were:

    (1) Mid-90s- not using DL 75k mile award for 2 tix from DCA-OGG in F (plus car rental I think)

    (2) In 2018, failing to book a couple of Marriott “meetings” before the rules changed which would have earned 20 EQN that I needed to qualify for my 10th year of Plat status (needed for lifetime Marriott Plat)

    (3) Letting numerous UA RPUs and GPUs expire instead of giving them to friends and family.

    (4) Not making better use of WN CPs (though I know this is a common problem for wage slaves with families)

    (5) The biggest – waiting until this year to get Amex Blue Plus and Chase Freedom Unlimited cards which allow me to earn 2/$1 and 1.5/$1 on everyday spend. Given my average spend I’ve probably missed out on 200k in transferable points over the past 10 years.

    Hopefully there will be another nostalgia column soon on things we miss the most…

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